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Volumn 48, Issue 31, 2009, Pages 5638-5641

Hydrogen-bond control in axially chiral styrenes: Selective synthesis of enantiomerically pure c2-symmetric paracyclophanes

Author keywords

C2 symmetry; Cyclophanes; Hydrogen bonds; Metathesis; Planar chirality

Indexed keywords

AXIAL CHIRALITY; C2 SYMMETRY; CYCLOPHANES; DIPHENOLS; METATHESIS; OXYGEN ATOM; PLANAR CHIRALITY; SELECTIVE SYNTHESIS; STEREOSELECTIVE FORMATION; STYRENE DERIVATIVES; SYNTHETIC PROBLEM;

EID: 70349912194     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200901974     Document Type: Article
Times cited : (65)

References (28)
  • 4
    • 0345643345 scopus 로고    scopus 로고
    • A decamethylene ansa bridge is short enough to suppress the flipping of this chain over the benzene ring: D. H. Hochmuth, W. A. Konig, Tetrahedron: Asymmetry 1999, 10, 1089-1097
    • A decamethylene ansa bridge is short enough to suppress the flipping of this chain over the benzene ring: D. H. Hochmuth, W. A. Konig, Tetrahedron: Asymmetry 1999, 10, 1089-1097.
  • 6
    • 0000136682 scopus 로고
    • For leading references, see: a
    • For leading references, see: a) D. J. Cram, H. U. Daeniker, J. Am. Chem. Soc. 1954, 76, 2743-2752;
    • (1954) J. Am. Chem. Soc , vol.76 , pp. 2743-2752
    • Cram, D.J.1    Daeniker, H.U.2
  • 24
    • 70349950213 scopus 로고    scopus 로고
    • The enantiomeric purity of the cyclized products (12,14,15-24) was confirmed by HPLC analysis on a chiral phase and comparison with the HPLC traces of the corresponding racemic compounds.
    • The enantiomeric purity of the cyclized products (12,14,15-24) was confirmed by HPLC analysis on a chiral phase and comparison with the HPLC traces of the corresponding racemic compounds.
  • 25
    • 70349951798 scopus 로고    scopus 로고
    • CCDC 727141 (12) and 727142 (14) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.ukJdata- request/cif.
    • CCDC 727141 (12) and 727142 (14) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.ukJdata- request/cif.
  • 26
    • 70349940836 scopus 로고    scopus 로고
    • For the preparation of tetraene 13, see the Supporting Information.
    • For the preparation of tetraene 13, see the Supporting Information.
  • 27
    • 70349937561 scopus 로고    scopus 로고
    • 1H NMR spectra. The signals of the protons attached to the newly formed C=C bond appeared at higher fields in comparison with those of the benzene analogues (12: δ = 5.26, 15: δ = 4.97). This tendency could be attributed to the stronger anisotropic effect of a naphthalene system relative to that of a benzene ring and/or to the closer spatial relationship of the vinyl hydrogen atoms to the π-electron cloud in the naphthalene system; see: a) T. Kusumi, H. Takahashi, T. Hashimoto, Y. Kan, Y. Asamawa, Chem. Lett. 1994, 1093-1094;
    • 1H NMR spectra. The signals of the protons attached to the newly formed C=C bond appeared at higher fields in comparison with those of the benzene analogues (12: δ = 5.26, 15: δ = 4.97). This tendency could be attributed to the stronger anisotropic effect of a naphthalene system relative to that of a benzene ring and/or to the closer spatial relationship of the vinyl hydrogen atoms to the π-electron cloud in the naphthalene system; see: a) T. Kusumi, H. Takahashi, T. Hashimoto, Y. Kan, Y. Asamawa, Chem. Lett. 1994, 1093-1094;


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.